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I would look st upgrading to SBS 2003, remote support and working is much improved in this version. I expect that you will, at the very least, need to look to upgrade the memory on the server for this.

I would upgrade the workstations to windows XP or look at Linspire as a cheaper alternative. You may be able to get away with increasing the memory and replacing the HDD in the workstations rather than replacement.

Not sure if your dialup is modem or ADSL, I would suggest upgrading satellites to ADSL if do already. Perhaps looking at the ADSL bandwidth at the main office also. You may need to look at an ADSL router supporting VPN from the satellite offices perhaps.

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I concur - SBS2003
If your on a budget - a nice mix is SBS2003 with a Terminal Server sitting beside it.
This would mean buying another server but there are benefits in other areas.
This would allow you to not bother with upgrading the desktops and could be a potential saving - this will also simplify putting in place policys and access controls as you will only have to bother with the Terminal server.
cheers
Steve

Sorry to answer a question with questions but you're not giving much to go on in terms of requirements. Usually if management wants an upgrade they don't want to know what kind of server you're going to give them, how much RAM the workstations are going go have or even how fast or secure it's going to be. They want to know what an upgrade is going to give them in features and how much it's going to cost. So how about starting there.
Do you have any requirements gathered? Depending on what they want you could be buying a new Linux/Samba server and Firewall/VPN or a new Win2K3 server w/ Sharepoint...

If you truly have the option to redesign, then go all the way. Obviously, you need to know the budget first. I realize in small companies they tend to start from the other side and ask how much is it going to cost, and when they are blown away by the amount, they start wanting to defer and/or eliminate things.
But assuming you truly have an open slate, I believe the best approach to take is to determine what your applications for a server environment. The app's you indicated could just as easily be Linux type things and certainly you would save some dollars (ie. the office suite). You didn't mention anything about financials or other ERP apps.
In a perfect world, this is what I would do...simplify. I have no particular bias for/against either Microsoft or Linux. Just the bottomline.
Start with a Network architecture (includes Internet)that is compatible with new/emerging technologies (ie. voice/data convergence). If a private IP network is to expensive, then setup a VPN using DSL/Cable and realize you will have ongoing management and performance related issues to deal with. A number of companies now provide private IP based WAN's that are very affordable and have SLA's (stay away from frame relay).
Next, incoporate a managed network security service (about $1k for hardware and $300 - $500/mo for service) that addresses not only firewall, but intrusion detection, Network level Anti-SPAM & Anti-Virus, privacy, content, acceptable use policy, remote client support, etc. Some even handle email which for 50 - 60 users would be just fine unless you have application integration issues or unusually high volume. Depending on the final network config, you could deploy a network security device at all locations.
As to servers, you could probably go with Linux/SAMBA on either Intel or IBM's eServer power5 technology and have a much more cost effective and "reliable" solution. An integrated UPS solution goes without saying.
As to workstations, I think solid values are available for under $1k/workstation and I would use the end of the year to negotiate an extra special deal. On software, Iwould look at desktop SUSE and the Openoffice products, but would probalby settle on WXP Pro and use non Microsft desktop apps both for reduced cost and increased security(ie. browser firefox instead of IE, Thurderbird instead of Exchange/Outlook, Openoffice instead of MS Office). For desktop security, I would look at Sophos instead of Norton.
As a final point, consider incorporating a new IP based PBX (ie. like 3Com NBX line)to replace your existing phone system. It could even be extended to the remote offices depending on the network you ultimately implement. And just in case you forgot, be sure to upgrade your network switch or hub to at least a 10/100 switch and probably 10/100/1000 since you won't get to do this again in the near future.
I haven't touched on everything, but I think you get the idea and hopefully some useful suggestions

I am of the Mind what is your main goal
how much do you have to spend
is it just hardware you are upgrading or are you truly upgrading all the network. (hardware,os, policies,Active dir,)
you have been given a clean slate if I am right in what you say.
think on how to make it work for the bosses then work for you.

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